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$118+ Cheap flights from Chicago (CHI) to Winnipeg (YWG)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
nov. 25 — dic. 21
lun. 11/25
lun. 12/2
1 adult, Economy
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The best prices from Chicago to Winnipeg are usually found in March or September, booked 46 days in advance, depart on a Thursday or Wednesday and return on a Wednesday

Cheap flight deals from Chicago to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated noviembre 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

April

Cheapest in

March

Round-trip from

$337
(Kiwi.com)

One-way from

$118
(Kiwi.com)
Provider with most accurate pricing for Chicago (CHI)-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Winnipeg flights.
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High demand for flights, 26% potential price rise
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Best time to find cheap flights, 61% potential price drop
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From Chicago (CHI) to Winnipeg
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One-way flight from Chicago (CHI) to Winnipeg
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Find flight deals from Chicago to Winnipeg

Cheapest flights from Chicago to Winnipeg
Explore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on noviembre 20, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/27:39 pmORD - YWG
2 stops25h 30mMultiple Airlines
lun. 12/97:30 amYWG - ORD
1 stop13h 40mMultiple Airlines
Deal found 11/19$337
This Kiwi.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/3012:55 pmMDW - YWG
2 stops8h 14mMultiple Airlines
vie. 12/67:30 amYWG - MDW
1 stop9h 42mMultiple Airlines
Deal found 11/19$404
This Air Canada deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/129:50 amORD - YWG
1 stop7h 18mAir Canada
lun. 12/1611:00 amYWG - ORD
1 stop8h 32mAir Canada
Deal found 11/19$474
This Delta deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/167:59 pmORD - YWG
2 stops15h 46mDelta
lun. 1/65:37 pmYWG - ORD
1 stop4h 21mDelta
Deal found 11/20$501
This Booking.com deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/1312:05 pmMDW - YWG
2 stops9h 04mPorter Airlines
lun. 12/1611:35 amYWG - MDW
2 stops22h 45mPorter Airlines
Deal found 11/20$530
This United Airlines deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/127:10 amORD - YWG
1 stop6h 17mUnited Airlines
lun. 12/167:30 amYWG - ORD
2 stops24h 23mUnited Airlines
Deal found 11/19$548
This CheapTicketsDeal deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/169:38 amMDW - YWG
1 stop26h 07mWestJet
lun. 1/66:55 amYWG - MDW
1 stop10h 52mWestJet
Deal found 11/20$575
This Delta deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/137:14 pmMDW - YWG
1 stop4h 20mDelta
lun. 12/1612:35 pmYWG - MDW
1 stop5h 57mDelta
Deal found 11/20$609
This WestJet deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/167:05 amORD - YWG
2 stops8h 29mWestJet
lun. 1/65:00 amYWG - ORD
2 stops15h 53mWestJet
Deal found 11/19$700
This Aeromexico deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/11:00 amORD - YWG
2 stops34h 25mAeromexico
mié. 12/48:00 pmYWG - ORD
2 stops27h 14mAeromexico
Deal found 11/19$2,372

Find flights from Chicago to Winnipeg within your budget

Customize your flight search to find flights from Chicago to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,629,791 searches. Data last updated noviembre 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun. 12/2

7:39 pm-9:09 pm

2 stops25h 30m

Winnipeg

lun. 12/9

7:30 am-9:10 pm

1 stop13h 40m

$337

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

sáb. 11/30

12:55 pm-9:09 pm

2 stops8h 14m

Winnipeg

vie. 12/6

7:30 am-5:12 pm

1 stop9h 42m

$404

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

jue. 12/12

9:50 am-5:08 pm

1 stop7h 18m

Winnipeg

lun. 12/16

11:00 am-7:32 pm

1 stop8h 32m

$474

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun. 12/16

7:59 pm-11:45 am

2 stops15h 46m

Winnipeg

lun. 1/6

5:37 pm-9:58 pm

1 stop4h 21m

$501

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

vie. 1/17

7:10 am-1:27 pm

1 stop6h 17m

Winnipeg

dom. 1/19

2:15 pm-4:51 pm

Nonstop2h 36m

$529

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

vie. 12/13

12:05 pm-9:09 pm

2 stops9h 04m

Winnipeg

lun. 12/16

11:35 am-10:20 am

2 stops22h 45m

$530

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

mar. 1/14

10:19 am-4:47 pm

1 stop6h 28m

Winnipeg

dom. 1/19

12:45 pm-5:47 pm

1 stop5h 02m

$544

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

lun. 12/16

9:38 am-11:45 am

1 stop26h 07m

Winnipeg

lun. 1/6

6:55 am-5:47 pm

1 stop10h 52m

$575

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun. 2/10

6:55 am-3:34 pm

2 stops8h 39m

Winnipeg

dom. 2/16

6:20 am-3:56 pm

1 stop9h 36m

$600

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

dom. 12/1

1:00 am-11:25 am

2 stops34h 25m

Winnipeg

mié. 12/4

8:00 pm-11:14 pm

2 stops27h 14m

$2,372

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 20 results
1
2

Compare providers for flights from Chicago to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Winnipeg in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago to Winnipeg

Get recent, data-driven insights about flights from Chicago to Winnipeg including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Chicago to Winnipeg?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Winnipeg. Price data was last updated on November 15, 2024.

The price you pay for your flight from Chicago to Winnipeg may vary depending on when you book. For the best chance of a lower fare, look to book 45 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Winnipeg?

Currently, September is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $339). Flying from Chicago to Winnipeg in February is currently the most expensive (average of $516). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to YWG?

Find hourly flight availability from Chicago to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated noviembre 20, 2024.

One of the essential ways to save on airfare from Chicago to Winnipeg is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 18% on airfare.

What is the cheapest day to fly from Chicago to Winnipeg?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Winnipeg. Price data was last updated on November 18, 2024.

Travelers seeking maximum savings on their Chicago to Winnipeg flight should consider departing on Thursday mornings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Winnipeg

Explore weekly flight availability from Chicago to Winnipeg. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated noviembre 20, 2024.

The most flights from CHI to YWG are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated noviembre 20, 2024.
See what other customers who have flown with United Airlines, WestJet and Porter Airlines from Chicago to Winnipeg have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,756 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,756 reviews
Delta
8.0
Very good
8,756 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Porter Airlines
7.8
Good
288 reviews
Delta
8.0
Very good
8,756 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Aeromexico
7.5
Good
2,004 reviews
Delta
8.0
Very good
8,756 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines
7.4
Good
9,171 reviews
Delta
8.0
Very good
8,756 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

WestJet
7.3
Good
2,811 reviews
Delta
8.0
Very good
8,756 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Winnipeg from Chicago?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago. On average, Winnipeg has 3 inbound flights from Chicago per day from 3 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • What are the cheapest airlines flying from Chicago to Winnipeg round-trip?

    Flying on Air Canada is currently your cheapest option to Winnipeg, with prices starting at $474. Additional round-trip tickets that might be worth considering are offered by United Airlines and Porter Airlines, with the lowest prices starting at $524 and $530, respectively. These flights start at 11% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Winnipeg one-way?

    One-way options have recently been found by users for as low as $191 on Porter Airlines. Other airlines that offer cheap prices include Air Canada from $207 and WestJet from $238 one-way.

  • What are the most reliable airlines from Chicago to Winnipeg?

    The top 3 most reliable airlines when flying from Chicago to Winnipeg are SkyWest Airlines (87%), Air Canada (87%) and United Airlines (87%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $220. On average you can expect to pay $752. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $293.

  • Can I find deals for flights from Chicago to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Chicago to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Winnipeg.

  • Can I find deals for business class flights from Chicago to Winnipeg?

    Yes. Cheapflights offers flight deals from Chicago to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Winnipeg?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $339). Flying from Chicago to Winnipeg in February is currently the most expensive (average of $516). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Winnipeg flights
Midway to Winnipeg flights
St. Louis to Winnipeg flights

Top 3 airlines flying from Chicago to Winnipeg

Discover the top 3 airlines that operate flights from Chicago to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,629,791 searches. Data last updated noviembre 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$219Average$609FlexibilityNo cancel feeOn-time67%
DeltaCheapest$510Average$636FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$535Average$735FlexibilityNo cancel feeOn-time69%
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